1,2-Dichloroethane → 5-(2-morpholinoethoxy)-1H-indole-3-carboxaldehyde

HRID 1749736Notes

Reaction equation

HRID 1749736 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][CH2:11][CH2:12][N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[CH:7][CH:8]=2)C=[CH:2]1.P(Cl)(Cl)(Cl)=O.[OH-:24].[K+].Cl.Cl[CH2:28][CH2:29]Cl>CN(C)C=O>[O:16]1[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][O:10][C:6]2[CH:7]=[C:8]3[C:9](=[CH:4][CH:5]=2)[NH:1][CH:2]=[C:28]3[CH:29]=[O:24])[CH2:14][CH2:15]1

Participants

7

Reactant 5

HCID 111,2-Dichloroethane2×HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24813Phosphorus oxychlorideHCID 221354424-[2-(1H-indol-5-yloxy)ethyl]morpholine

Product 1

HCID 866819325-(2-morpholinoethoxy)-1H-indole-3-carboxaldehydeYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under an argon atmosphere, a solution of 4-[2-(1H-indol-5-yloxy)ethyl]morpholine (0.12 g, 0.5 mmol) in 1,2-dichloroethane (2.0 mL) was added dropwise with a solution of phosphorus oxychloride (0.1 mL) and N,N-dimethylformamide (0.1 mL) in 1,2-dichloroethane (1.0 mL). The mixture was stirred at room temperature for 1 hour, and then added with 3 N aqueous potassium hydroxide, and the mixture was stirred at 60° C. for 2 hours. The aqueous layer was adjusted to pH 7 with 3 N hydrochloric acid, and then extracted with ethyl acetate. The resulting organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, the residue was suspended in a mixed solvent of ethyl acetate and hexane and thereby washed to obtain 5-(2-morpholinoethoxy)-1H-indole-3-carboxaldehyde (0.068 g, 50%).

Workup

  1. stirringthe mixture was stirred at 60° C. for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe resulting organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washwashed

Sources & evidence

ORD record
ord-f26ea1b158154daf8e01618c78fd3285
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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